Holiday Rentals in Brookline, MA

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Brookline, MA holiday rentals
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1019 Holiday rentals and Airbnb in Brookline, MA

Best family friendly Brookline, MA holiday rentals

Among the 1019 accommodations in Brookline, MA, here are the 4 best family friendly rentals

Luxe 3bd Allston - Brookline, MA
No reviews

Luxe 3bd Allston

apartment, Boston
This family-friendly Allston flat is conveniently located 2.6 kilometres from Harvard Square and 2.3 kilometres from Harvard University, with John F. Kennedy Park 1.6 kilometres away and Brattle Theatre 2 kilometres distant.
This spacious 138 square metre apartment offers three bedrooms, two bathrooms, air conditioning, complimentary WiFi, and free private parking, accommodating up to 14 guests with a fully equipped kitchen including a fridge, microwave oven, and dishwasher.
3br2bth Parking Cambridge Boston W&d Subway Ac - Brookline, MA
9.8 16 reviews

3br2bth Parking Cambridge Boston W&d Subway Ac

house, Somerville
This Somerville holiday home is situated near Inman Square, approximately 1.9km from the Central Square Theatre, 2.3km from the Massachusetts Institute of Technology (MIT), and a short distance from Cambridge College and the Peabody Museum.
The 102 square metre property offers three bedrooms, two bathrooms, sleeps thirteen guests, and includes free Wi-Fi, private parking, and a fully equipped kitchen with a dishwasher.
Historic Brownstone Townhouse, 7 Beds/3.5 Baths, Fenway Boston - Brookline, MA
10 180 reviews

Historic Brownstone Townhouse, 7 Beds/3.5 Baths, Fenway Boston

apartment, Boston
This 7-bedroom house is conveniently located in the Fenway–Kenmore district, just a short walk from Fenway Park, Boston University, and the Longwood Medical Area. This property consistently receives excellent ratings for location, cleanliness, and overall user experience.
The spacious 372 square metre house comfortably accommodates up to 16 guests. Enjoy access to a fully equipped kitchen, a private patio, and a garden, ideal for relaxing after a day exploring the city.
Charming Tree Top Victorian - Two Bedroom Retreat - Brookline, MA
10 18 reviews

Charming Tree Top Victorian - Two Bedroom Retreat

apartment, Boston
This family-friendly flat is located in Jamaica Plain, a neighbourhood in Boston, just 3km from Franklin Park Zoo, Brigham and Women's Hospital, and Longwood Medical Area. It has received excellent user ratings, making it a popular choice for travellers.
The apartment is spacious, with 2 bedrooms, 1 bathroom, and a floor area of 149 square metres, comfortably accommodating up to 4 guests. A range of amenities are available, including a swimming pool, tennis court, garden, and barbecue grills, ensuring a relaxing and enjoyable stay.

Best Brookline, MA holiday rentals with parking

Central Space To Balance Life Work Play 7 Sleeps - Brookline, MA
9.4 18 reviews

Central Space To Balance Life Work Play 7 Sleeps

apartment, Cambridge
This Cambridge apartment, situated in a central location, is a 3-minute walk from the Central Square Theatre, an 11-minute walk from the Massachusetts Institute of Technology (MIT), and close to Inman Square and the University of Cambridge.
This 93 square metre (1000 square foot) self-catering property features two bedrooms sleeping up to seven guests, two bathrooms, a fully equipped kitchen, in-unit laundry, free Wi-Fi, on-site fitness centre, garden, and parking, making it ideal for groups visiting Cambridge.
Luxury 3br | Free Parking | Harvard/bu | Roku Tv - Brookline, MA
9.4 37 reviews

Luxury 3br | Free Parking | Harvard/bu | Roku Tv

apartment, Boston
This 3-bedroom flat is situated in Boston's Allston district, a mere 1.9 kilometres from Downtown Boston and a short distance from Harvard University and Fenway Park.
This 121 square metre apartment accommodates up to eight guests and features high-speed Wi-Fi, air conditioning, and a fully equipped kitchen with modern appliances.
Free Parking At 1 Bed Basement Apt, Near Bu & Mit - Brookline, MA
8.6 35 reviews

Free Parking At 1 Bed Basement Apt, Near Bu & Mit

apartment, Boston
This Boston flat is situated in the Fenway-Kenmore neighbourhood, close to Boston University and Kenmore Square, offering easy access to public transport and proximity to Fenway Park and TD Garden.
The self-contained basement apartment sleeps four, features a kitchen with fridge, microwave, and dishwasher, plus air conditioning, parking, and is within walking distance of local shops and restaurants.
Free Parking Spot  In Front Of Subway - Location - Brookline, MA
9.9 56 reviews

Free Parking Spot In Front Of Subway - Location

apartment, Boston
This Boston studio flat enjoys a superb location directly opposite a T-station, providing easy access to Fenway Park (approx. 2.4km by T), Back Bay (a short T journey), and Boston University (approx. 2.4km by T).
The self-contained apartment, sleeping up to two guests, includes a fully equipped kitchen (fridge, freezer, microwave, dishwasher), air conditioning, free parking nearby, on-site laundry, and self check-in.

Frequently asked questions about holiday rentals in Brookline, MA

  • What should a first-time visitor not miss in Brookline, MA?

    Brookline is known for its lovely parks and green spaces, so a visit to the picturesque Larz Anderson Park with its beautiful gardens and The Larz Anderson Auto Museum is a must. You should also check out the Brookline Public Library for its beautiful architecture and cultural events.
  • What are the best Airbnb and holiday rentals in Brookline, MA?

  • Which neighborhood in Brookline, MA should you consider for a vacation rental?

    The Coolidge Corner neighbourhood is a great choice for a vacation rental. It's a lively area with lots of shops, restaurants, and cafes, and it's within easy walking distance of the Green Line subway station.
  • What are the most popular Airbnbs in Brookline, MA?

  • What are the top family-friendly attractions in Brookline, MA?

    The Brookline Recreation Department offers a variety of family-friendly activities throughout the year, including summer camps, swimming lessons, and sports leagues. The Brookline Public Library also hosts many events for children, including story time and craft sessions.
  • What are the best holiday rentals with a pool in Brookline, MA?

  • When is the best time to book a vacation rental in Brookline, MA?

    The best time to book a vacation rental in Brookline is during the shoulder seasons, in spring or autumn. The weather is still pleasant, but the crowds are smaller and prices are lower.
  • What are the best rentals for families and kids in Brookline, MA?

  • What events or festivals should visitors check out in and around Brookline, MA?

    The Brookline Farmers Market is a popular event held every Saturday from June to October, offering fresh produce, local crafts, and live music. The annual Brookline Open Studios event is a great chance to see the work of local artists in their studios.
  • What are the best rentals or Airbnbs with a jacuzzi in Brookline, MA?

    The best vacation rentals or Airbnb with a jacuzzi in Brookline, MA are Ultraluxe Apt In Boston Brownstone In Prime Area, Beautiful Clean Bright Corner Unit and Walking To Fenway Sunny Perfect Home.

  • What are the best budget-friendly activities in Brookline, MA?

    Brookline has many free or low-cost activities to enjoy. Take a walk or cycle along the Emerald Necklace, a series of parks and green spaces that connect Brookline to Boston. The Brookline Public Library offers free events and programmes throughout the year.
  • What are the best restaurants with local dishes in Brookline, MA?

    For a taste of local cuisine, try The Fireplace in Coolidge Corner. They offer classic New England dishes with a modern twist. The Publick House in Brookline Village serves traditional American comfort food.
  • What are the best walking or cycling routes in Brookline, MA?

    The Emerald Necklace is a great option for walking or cycling. It's a 10 km long park system that connects Brookline to Boston. The Charles River Esplanade is another popular walking and cycling route, offering beautiful views of the Charles River.
  • Are there pet-friendly attractions in Brookline, MA?

    Many of Brookline's parks are pet-friendly, including Larz Anderson Park and The Muddy River Reservation. The Brookline Farmers Market also welcomes well-behaved dogs.
  • What are the benefits of choosing a vacation rental in Brookline, MA?

    Vacation rentals offer more space and privacy than a hotel room. They're also often located in more residential areas, giving you a chance to experience local life.
  • What are the top sports attractions and facilities in Brookline, MA?

    While Brookline doesn't have a major sports stadium, it's close to Boston, home to many professional sports teams. The Boston Marathon also passes through Brookline every year.

Popular destinations

Best Brookline, MA holiday rentals with a balcony

4br/4ba | Parking + Chef’s Kitchen | Near Bu/bc - Brookline, MA
10 1 review

4br/4ba | Parking + Chef’s Kitchen | Near Bu/bc

house, Brookline
This penthouse is located in Coolidge Corner, Brookline, offering convenient access to Boston landmarks such as Fenway Park, located 3.7 kilometres away, and Boston University, 4.3 kilometres away.
This spacious 1000 square meter property features a 4-bedroom, 4-bathroom layout accommodating up to 10 guests, with amenities including a fridge, microwave oven, dishwasher, air conditioning, a balcony, and complimentary Wi-Fi.
A Stylish Stay W/ A Queen Bed, Heated Floors.. #14 - Brookline, MA
9.6 1 review

A Stylish Stay W/ A Queen Bed, Heated Floors.. #14

apartment, Brookline
Apartment listing with an excellent rating of 96% based on 1 reviews. You will stay in Brookline.
Services and facilities: a wheelchair friendly access, a kitchen and an iron. Take advantage of the air conditioning in this apartment!
Symphony Suites By Thatch - Brookline, MA
9.2 6 reviews

Symphony Suites By Thatch

apartment, Boston
Accommodation with an excellent rating of 92% based on 6 reviews. You will be in Boston.
Services and facilities include a kitchen, a fridge and an access for persons with reduced mobility. Take advantage of the air conditioning in this apartment in Boston.
Relaxing 2-br Townhome Steps To Mit, Harvard, T Red Line, Food & More! - Brookline, MA
9.4 10 reviews

Relaxing 2-br Townhome Steps To Mit, Harvard, T Red Line, Food & More!

apartment, Cambridge
This pet-friendly Cambridge house, situated in Cambridgeport, is a 0.64km drive from Harvard Square and a 0.8km drive from Fenway Park, offering convenient access to major attractions.
The 102 square metre property boasts two bedrooms, two bathrooms, sleeps five, and includes a private garden, terrace, spa, parking, and a fully equipped kitchen with appliances such as a dishwasher and microwave; nearby water activities include kayaking, boating and sailing.

Best Brookline, MA holiday rentals with air conditioning

A Stylish Stay W/ A Queen Bed, Heated Floors.. #34 - Brookline, MA
9.1 3 reviews

A Stylish Stay W/ A Queen Bed, Heated Floors.. #34

apartment, Brookline
Apartment rental listing with an excellent rating of 91% based on 3 reviews. Your accommodation will be based in Brookline.
Services and facilities: a dish washer, a washing machine and an elevator. This apartment in Brookline also has air conditioning!
New Spacious 2b2b Apartment, One Free Parking Spot - Brookline, MA
9.9 287 reviews

New Spacious 2b2b Apartment, One Free Parking Spot

apartment, Brookline
This Brookline apartment is ideally located near Coolidge Corner, offering easy access to Boston's T-system and proximity to the Longwood Medical Area, Fenway Park, and Boston University.
The recently renovated two-bedroom, two-bathroom flat sleeps six guests and includes a fully equipped kitchen, free parking, and individual climate control; pet-friendly (surcharge applies).
Luxury 3br | Free Parking | Harvard/bu | Roku Tv - Brookline, MA
9.5 31 reviews

Luxury 3br | Free Parking | Harvard/bu | Roku Tv

apartment, Boston
This three-bedroom flat is situated in Boston's Allston district, a mere 19 kilometres from Downtown Boston and minutes from Harvard University, Fenway Park, and the Charles River.
This family-friendly 121 square metre residence accommodates up to eight guests and offers high-speed Wi-Fi, air conditioning, and a kitchen equipped with a fridge, freezer, microwave oven, and dishwasher.
Luxury 3br 2ba Boston Penthouse - Brookline, MA
9.0 5 reviews

Luxury 3br 2ba Boston Penthouse

apartment, Boston
This luxury 3-bedroom, 2-bathroom Boston penthouse boasts a prime location, situated 3.2 kilometres from Fenway Park and a 18-minute walk to the Boston Museum of Fine Arts.
This spacious 148 square metre apartment sleeps up to 11 guests and offers a fully equipped kitchen with a dishwasher and oven, complimentary WiFi, and air conditioning.
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